Siegel's first professional broadcasting job was at
WGLI in
Babylon, New York, where he "did morning newscasts and a show that was part phone-ins, part
Top Forty, all under the pseudonym Bob Charles." After graduate school, he worked for
WRVR in New York from 1971 to 1976. Siegel was hired as a newscaster for NPR in
Washington, D.C., in 1976, From 1979 to 1983 he was based in London, making him the first NPR staffer to be based overseas. Upon his return to America, he became the director of the News and Information Department, and was responsible for overseeing production of both
All Things Considered and
Morning Edition, as well as the creation of
Weekend Edition. Siegel won three
Silver Batons from Alfred I. DuPont-Columbia University and the American Bar Association's
Silver Gavel Award. Siegel has made cameo appearances in several television shows, including
The Simpsons,
Northern Exposure,
BoJack Horseman and the film
Yesterday Was a Lie. For the weeks of June 5, 2018, and February 17, 2020, Siegel guest-hosted NPR's
On Point. Since September 2025, he has served as a host of The Opinions – The New York Times podcast. == Personal life ==